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Acetanilide → 3-Anilino-4-fluorobenzyl 2,2-dimethyl-2-(4-ethoxyphenyl)ethyl ether

HRID 638634
Notes
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Reaction equation

HRID 638634 reaction equation
[CH3:1][C:2]([CH3:23])([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH3:22])=[CH:16][CH:15]=1)[CH2:3][O:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([F:12])=[C:8](Br)[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].C([NH:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)(=O)C>CN(C)C=O>[CH3:1][C:2]([CH3:23])([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH3:22])=[CH:16][CH:15]=1)[CH2:3][O:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([F:12])=[C:8]([NH:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 904AcetanilideHCID 11430Potassium CarbonateHCID 134881903-Bromo-4-fluorobenzyl 2,2-dimethyl-2-(4-ethoxyphenyl)ethyl ether

Product 1

HCID 133638483-Anilino-4-fluorobenzyl 2,2-dimethyl-2-(4-ethoxyphenyl)ethyl ether

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

2.37 Grams of 3-bromo-4-fluorobenzyl 2,2-dimethyl-2-(4-ethoxyphenyl)ethyl ether, 0.95 g of potassium carbonate, 1.01 g of acetanilide, 10 ml of dimethylformamide and 250 mg of cuprous chloride were mixed and stirred at 140° C. for 40 hours in a nitrogen stream. The reaction mixture was poured into ice water and extracted with ethyl acetate. The ethyl acetate layer was washed with an aqueous sodium chloride liquor, and after removing the solvent by evaporation, the residual oil was dissolved in a 20% ethanol solution of potassium hydroxide (2 times by mole) and refluxed for 30 minutes. The reaction solution was then poured into ice water and extracted with ether. The ether layer was washed with an aqueous sodium chloride liquor and dried over anhydrous magnesium sulfate, and the solvent was removed by evaporation. The residual oil was separation-purified by column chromatography on silica gel to obtain 1.05 g of 3-anilino-4-fluorobenzyl 2,2-dimethyl-2-(4-ethoxyphenyl)ethyl ether.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with an aqueous sodium chloride liquor
  3. customafter removing the solvent
  4. customby evaporation
  5. dissolutionthe residual oil was dissolved in a 20% ethanol solution of potassium hydroxide (2 times by mole)
  6. temperaturerefluxed for 30 minutes
  7. additionThe reaction solution was then poured into ice water
  8. extractionextracted with ether
  9. washThe ether layer was washed with an aqueous sodium chloride liquor
  10. dry with materialdried over anhydrous magnesium sulfate
  11. customthe solvent was removed by evaporation
  12. customThe residual oil was separation-purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-9e80d37ee8754ea2978e2c48634843e2
Source dataset
uspto-grants-1985_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04562213

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes